Midterm Exam Three

 

CHM 231

 

There are 25 multiple choice questions followed by a periodic chart.  Note your best answer on the scanner sheet.  Turn in the scanner sheet.  You may take the exam with you.

1.                  Which of the following is the strongest acid?

 

 

2.                  Which of the following is a tertiary amine?

 

 

 

3.                  Of the following, the structure of pyridine is:

 

 

 

 

4.                  Of the following, which is the weakest base?

 

 

 

 

5.                  The mechanism of the following reaction is most likely:

 

 

 

A.                 SN1

B.                 SN2

C.                 E1

D.                 E2

 

 

 

 

 

 

 

 

 

 

6.                  Which of the following suggested starting materials cannot be used to give the indicated product in the following reaction?

 

 

 

 

 

 

 

 

 

 

 

 

7.                  Which of the following reagents is not useful for the indicated reaction?

 

 

 

A.                 NaBH4

B.                 LiAlH4

C.                 H2/catalyst

D.                 NaH

E.                  At least two of the above could not be used

 

8.                  Reaction of a large excess of butanamine with iodomethane will yield, as the major product:

 

 

 

 

 

 

 

 

 

9.                  Which of the following is not an alkaloid?

 

 

 

10.              The following structure is an example of:

 

 

A.                 acetal

B.                 ketal

C.                 hemiacetal

D.                 hemiketal

 

 

11.              Addition of which of the following reagents to cyclohexanone is irreversible?

 

A.                 CH3MgBr

B.                 H2O

C.                 NH3

D.                 CH3OH

 

 

12.              Which reagent would be best for the following transformation?

 

 

A.                 HCl

B.                 PCC

C.                 Hydroxide ion

D.                 H2SO4

 

13.              Which of the following is a tertiary alcohol?

 

 

 

 

 

 

 

 

14.              The most acidic proton in the following structure is:

 

 

15.              Which of the following structures is a ketal?

 

 

16.              Of the following, the strongest base is:

 

 

17.              The product that is isolated from the following reaction is:

 

 

 

18.              Consider the following reaction.  The mechanism is most likely:

 

 

 

A.                 E1

B.                 E2

C.                 SN1

D.                 SN2

 

 

19.              The following reaction can be carried out using:

 

A.                 NaBH4

B.                 LiAlH4

C.                 H2/cat

D.                 Any of the above

 

20.              The following compound can be formed by the aldol reaction of which two starting materials?

 

 

 

 

 

21.              Which of the following would give a positive Tollens test (reaction with Ag2O)?

 

 

 

22.              The IUPAC name of the following compound is:

 

                       

 

A.                 4,4-dimethyl-2-hydroxypentanal

B.                 2-hydroxy-4,4-dimethylpentanal

C.                 2-hydroxy-4,4-dimethyl-1-pentanone

D.                 4,4-dimethyl-2-pentanoic acid

 

 

 

 

 

 

 

 

 

 

 

23.              The IUPAC name of the following compound is:

 

 

A.                 dimethylaminobenzene

B.                 N,N-dimethylaniline

C.                 N,N-dimethylaminobenzene

D.                 1,1-dimethylaminobenzene

 

 

24.              The reagent needed to carry out the following reaction is:

 

 

A.                 CuCl

B.                 NaCl

C.                 Cl2/FeCl3

D.                 AlCl3

 

 

25.              Which reaction of those below is the best way to prepare 4-methylpentanoic acid?